@Jamie ParkerAppreciate the effort and plan you are taking - it part of every plan is to re evaluate to move forwardHow much time have you spent compared to how much have you made?

If the purpose is to avoid probate, then everything should be in the trust.

Those are tiny, tiny obstacles compared to where this process succeeds or fails, and that is with the contracting. 

Compare that to the seller's staffing matrix and make adjustments as needed. 

For tax purposes, it’s about whether you pass the 750-hour rule, the 50% rule, and meet the material participation requirements.

This would allow us to have a clear bird-eye view of the various data in order to analyze and take decisions Second Point:I would prefer to manage it internally for confidentiality purposes.

What happens if you buy the duplex with a conventional loan with the purpose to build an ADU to move in shortly afterwards?

I wrote the above for informational purposes.

There are a lot of variables to consider so it's impossible to say if investing in one of those other markets would have been "better".However, I think you could make a stronger case that you have been (or would be) more successful with your real estate investing in Chicago compared to other markets.

I think I would probably talk to an attorney tbh these business purpose non regulated loans do not have rate locks that have to be honored legally.. they can and do change them unilaterally.. borrower accepts counters or declines and loan fails.